Trimethylsilyldiazomethane → HCID 69512394, compound

HRID 1909702Notes

Reaction equation

HRID 1909702 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20](=[O:26])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:30]>CO.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20](=[O:26])[CH2:21][CH2:22][C:23]([O:25][CH3:30])=[O:24])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 69512836HCID 69512836, compound

Product 1

HCID 69512394HCID 69512394, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-{(S)-2-[4-(4-chloro-phenyoxy)-phenoxymethyl]-pyrrolidin-1-yl}-4-oxo-butyric acid (d4) (500 mg, 1.2 mmol, 1 eq.) in a mixture of methanol (6 ml) and benzene (5 ml) was added dropwise TMSCHN2 (2 M in hexane, 3 ml, 6 mmol, 3 eq.) with stirring. The mixture was stirred until the starting acid was consumed by indication of yellow color persists). Then volatile material was removed under reduced pressure. The crude product thus obtained was forwarded to the next step without further purification.

Workup

  1. stirringThe mixture was stirred until the starting acid
  2. customwas consumed by indication of yellow color persists)
  3. customThen volatile material was removed under reduced pressure

Sources & evidence

ORD record
ord-80f0ea895ac34f49bc0a49f275f946d2
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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