(2S,4R)-ethyl 4-(dibenzylamino)-2-ethyl-1-methylcyclopentanecarboxylate → (2S,4R)-ethyl 4-amino-2-ethyl-1-methylcyclopentanecarboxylate

HRID 2204471Notes

Reaction equation

HRID 2204471 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]1[CH2:13][C:12]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C@H:11]([CH2:20][CH3:21])[CH2:10]1)C1C=CC=CC=1.C([N:36](CC1C=CC=CC=1)[C@H:37]1[CH2:41][C:40]([CH3:47])([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C@@H:39]([CH2:48][CH3:49])[CH2:38]1)C1C=CC=CC=1>>[NH2:8][C@@H:9]1[CH2:13][C:12]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C@H:11]([CH2:20][CH3:21])[CH2:10]1.[NH2:36][C@H:37]1[CH2:41][C:40]([CH3:47])([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C@@H:39]([CH2:48][CH3:49])[CH2:38]1

Participants

4

Reactant 2

HCID 58010117(2S,4R)-ethyl 4-(dibenzylamino)-2-ethyl-1-methylcyclopentanecarboxylateHCID 58010228(2R,4S)-ethyl 4-(dibenzylamino)-2-ethyl-1-methylcyclopentanecarboxylate

Product 2

HCID 58009848(2R,4S)-ethyl 4-amino-2-ethyl-1-methylcyclopentanecarboxylateHCID 58009886(2S,4R)-ethyl 4-amino-2-ethyl-1-methylcyclopentanecarboxylateYield 100%

Procedure

A mixture of (2R,4S)-ethyl 4-(dibenzylamino)-2-ethyl-1-methylcyclopentanecarboxylate and (2S,4R)-ethyl 4-(dibenzylamino)-2-ethyl-1-methylcyclopentanecarboxylate (0.864 g, 2.28 mmol) was debenzylated using General Procedure FF to give (2R,4S)-ethyl 4-amino-2-ethyl-1-methylcyclopentanecarboxylate and (2S,4R)-ethyl 4-amino-2-ethyl-1-methylcyclopentanecarboxylate (0.45 g, 100%). LC/MS (Table 2, Method a) Rt=1.55 min; MS m/z: 200 (M+H)+.

Sources & evidence

ORD record
ord-a44a270238ec4363891a15319a3186b3
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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