Methyl 3-(4-nitrophenyl)adamantane-1-carboxylate → Methyl 3-(4-aminophenyl)adamantane-1-carboxylate

HRID 1713840Notes

Reaction equation

HRID 1713840 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][C:12]([C:20]([O:22][CH3:23])=[O:21])([CH2:13]4)[CH2:11]2)[CH2:17]3)=[CH:6][CH:5]=1)([O-])=O.NC1C=CC(C2CCC(C(OC)=O)C2)=CC=1>>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][C:12]([C:20]([O:22][CH3:23])=[O:21])([CH2:13]4)[CH2:11]2)[CH2:17]3)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 2843498Methyl 3-(4-nitrophenyl)adamantane-1-carboxylateHCID 59464327Methyl 3-(4-aminophenyl)cyclopentanecarboxylate

Product 1

HCID 535215Methyl 3-(4-aminophenyl)adamantane-1-carboxylate

Procedure

Methyl 3-(4-Nitrophenyl)adamantane-1-carboxylate was reduced by the method of Intermediate 84, step (ii), to give the title compound (Intermediate 85); 1H NMR δ 6.99 (d, 2H), 6.51 (d, 2H), 4.80 (s, 2H), 3.59 (s, 3H), 2.17-2.10 (m, 2H), 1.87-1.79 (m, 6H), 1.77-1.72 (m, 4H), 1.69-1.63 (m, 2H); MS m/e M+MeCN 327.

Sources & evidence

ORD record
ord-0384344d94a64130be9ad66f7ece3f20
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…