(1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-ene-1-carboxamide → (1S)-1-Isopropyl-3-{4-[3-(methoxycarbonyl)phenyl]piperidin-1-yl}cyclopentane carboxylic acid

HRID 643576Notes

Reaction equation

HRID 643576 reaction equation
C(OC1C=CC(C(F)(F)F)=CC=1CNC([C@]1(C(C)C)CC(N2C(C)=CC=C2C)C=C1)=O)(C)(C)C.C([O:42][C:43]([C@@:45]1([CH:66]([CH3:68])[CH3:67])[CH2:49][CH2:48][CH:47]([N:50]2[CH2:55][CH2:54][CH:53]([C:56]3[CH:57]=[C:58]([CH:63]=[CH:64][CH:65]=3)[C:59]([O:61][CH3:62])=[O:60])[CH2:52][CH2:51]2)[CH2:46]1)=[O:44])C1C=CC=CC=1>>[CH:66]([C@:45]1([C:43]([OH:44])=[O:42])[CH2:49][CH2:48][CH:47]([N:50]2[CH2:55][CH2:54][CH:53]([C:56]3[CH:65]=[CH:64][CH:63]=[C:58]([C:59]([O:61][CH3:62])=[O:60])[CH:57]=3)[CH2:52][CH2:51]2)[CH2:46]1)([CH3:68])[CH3:67]

Participants

3

Reactant 2

HCID 58617139(1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-ene-1-carboxamideHCID 58617156Methyl 3-(1-{(3S)-3-[(benzyloxy)carbonyl]-3-isopropylcyclopentyl}piperidin-4-yl)benzoate

Product 1

HCID 58617140(1S)-1-Isopropyl-3-{4-[3-(methoxycarbonyl)phenyl]piperidin-1-yl}cyclopentane carboxylic acid

Procedure

(1S)-1-Isopropyl-3-{4-[3-(methoxycarbonyl)phenyl]piperidin-1-yl}cyclopentane carboxylic acid was synthesized as described for INTERMEDIATE 3 (procedure A, step F) using methyl 3-(1-{(3S)-3-[(benzyloxy)carbonyl]-3-isopropylcyclopentyl}piperidin-4-yl)benzoate as starting material. The desired was obtained as a 10:1 mixture of cis: trans around the cyclopentane ring.

Workup

  1. customThe desired was obtained as a 10:1 mixture of cis

Sources & evidence

ORD record
ord-53f357c5d18148e7a6144037c839078e
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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