Benzyl ether (Bn)
Protection :
-
-
BnBr, NaH, n-Bu4N+ I-
THF
0 °C to RT, 4.5 h, 98%
-
BnBr, KH, n-Bu4N+ I-
Et2O
RT, 2 h, 87%
-
BnBr, TMS2NK
THF
0 °C to RT, 20 min, 92%
-
TfOH, Cl3C(=NH)OBn
Et2O
RT, 10 h, 100%
-
BnBr, NaH
DMF
0 °C to RT, 19 h, 92%
-
BnBr, K2CO3
Acetone
Reflux, 24 h, 92%
Deprotection :
-
-
H2, Pd/C
EtOAc
RT, 11.5 h, 85%
H2, Pd/C
EtOAc
RT, 30 min, 97%
H2, Pd/C
EtOAc
RT, 45 min, 82%
H2, Pd/C
EtOAc
RT, 30 h, 98%
-
H2, Pd/C
MeOH
RT, 6 min, 74%
H2, Pd/C
MeOH
RT, 14 h, 81%
H2, Pd/C
MeOH
RT, 20 h, 89%
-
H2, Pd/C
EtOH
RT, 10 h, 82%
H2, Pd/C
EtOH
RT, 3 h, 95%
-
H2, Pd(OH)2/C
EtOH
RT, 23 h, 76%
-
H2, Pd(OH)2/C
EtOH, i-PrOH, MeOH
RT, 48 h, 96%
-
Li
EtOH, NH3, THF
Reflux, 60 min, 90%
-
Na
NH3, THF
-78 to -45 °C, 2 h, 100%
-
H2, Pd/C
AcOH, MeOH
20 h, 96%
-
H2, Pd(OH)2/C
EtOAc, EtOH
RT, 5 h, 67%
-
Li.DTBBP
THF
-78 °C, 3 h, 95%