Acetyl chloride → HCID 22859576, compound
Reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=3)[CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1.C(Cl)(=O)C>C(O)C>[OH:33][CH2:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]3[CH2:16][C@H:12]2[CH2:13][CH2:14][CH2:15][NH:11]2)=[CH:31][CH:30]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(4-hydroxymethylphenyl)-1H-indole (450 mg, 0.973 mmol) (see Preparation 39) in ethanol was reduced using catalytic hydrogenation as described in Example 35 except that no acetyl chloride was used in the reaction. This gave the title compound as an off-white powder, m.pt. 65°-69° C. (210 mg). Found: C,76.15; H,7.43; N,8.66; C20H22N2O.1/2H2O requires: C,76.16; H,7.35; N,8.88%.