(R)-methyl 5-(3-(3,3-difluoro-5-(hydroxymethyl)-2-oxopyrrolidin-1-yl)propyl)thiophene-2-carboxylate → methyl(R)-5-(3-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)propyl)thiophene-2-carboxylate

HRID 59688Notes

Reaction equation

HRID 59688 reaction equation
[F:1][C:2]1([F:22])[CH2:6][C@H:5]([CH2:7][OH:8])[N:4]([CH2:9][CH2:10][CH2:11][C:12]2[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=2)[C:3]1=[O:21].FC1(F)C[C@H](CO)N(CCCCCCC(OC)=O)C1=O>>[F:22][C:2]1([F:1])[CH2:6][C@H:5]([CH:7]=[O:8])[N:4]([CH2:9][CH2:10][CH2:11][C:12]2[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=2)[C:3]1=[O:21]

Participants

3

Reactant 2

HCID 90054431(R)-methyl 5-(3-(3,3-difluoro-5-(hydroxymethyl)-2-oxopyrrolidin-1-yl)propyl)thiophene-2-carboxylateHCID 90054523(R)-methyl 7-(3,3-difluoro-5-(hydroxymethyl)-2-oxopyrrolidin-1-yl)heptanoate

Product 1

HCID 90054427methyl(R)-5-(3-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)propyl)thiophene-2-carboxylate

Procedure

(R)-Methyl 5-(3-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)propyl)thiophene-2-carboxylate was prepared from 12f using the oxidation procedure (Step K) described for the preparation of intermediate 13a from intermediate 12a to afford the title intermediate (80 mg) as a pale yellow oil; TLC Rf 0.60 (solvent system: 7:93 v/v methanol-dichloromethane).

Sources & evidence

ORD record
ord-80cc36812edf4c4b9f2d337f5603bd04
Source dataset
uspto-grants-2016_09
Patent number
US09440919B2

Reaction notes

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