(R)-Tetrahydro-3-furoic acid → HCID 58303015, compound

HRID 587378Notes

Reaction equation

HRID 587378 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[O:25]1[CH2:29][CH2:28][CH:27]([C:30](O)=[O:31])[CH2:26]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:30]([CH:27]3[CH2:28][CH2:29][O:25][CH2:26]3)=[O:31])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 4661317(R)-Tetrahydro-3-furoic acidHCID 67233751[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Product 1

HCID 58303015HCID 58303015, compound

Procedure

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound [(3S,4R)-4-(4-chloro-phenyl)-1-(tetrahydro-furan-3-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from [(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester instead of [(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using rac-tetrahydro-3-furoic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as a light brown oil. MS m/e: 447.2 [M+H]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
  2. customwas obtained as a light brown oil

Sources & evidence

ORD record
ord-61fbec57e2b342558340363cbd9a938c
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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