Trimethylsilyldiazomethane → HCID 69512394, compound

HRID 750013Notes

Reaction equation

HRID 750013 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-343de1fab1214b81899c3591f7edc4fb
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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