tert-Butyldimethylsilyl chloride → HCID 57659765, compound

HRID 1011611Notes

Reaction equation

HRID 1011611 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[CH:9]1([C@H:12]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:15]([CH2:24][OH:25])[CH:14]([OH:26])[CH2:13]2)[CH2:11][CH2:10]1>N1C=CC=CC=1.C(Cl)Cl>[Si:5]([O:25][CH2:24][CH:15]1[CH:14]([OH:26])[CH2:13][C@@H:12]([CH:9]2[CH2:10][CH2:11]2)[N:16]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 57659761HCID 57659761, compound

Product 1

HCID 57659765HCID 57659765, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

TBSCl (1.35 g, 9.00 mmol) was added to a solution of (5S)-tert-butyl 5-cyclopropyl-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (32) (1.93 g, 7.50 mmol) in pyridine (15 mL) and the resulting solution was stirred at rt for 18 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed with 1 N aq. HCl (10 mL). The organic phase was dried (Na2SO4), filtered and concentrated under vacuum to give (5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-cyclopropyl-3-hydroxypyrrolidine-1-carboxylate (33). Retention time (min)=3.261 method [1], MS (m/z) 394.2 (M+Na)+.

Workup

  1. washwashed with 1 N aq. HCl (10 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3c6c6ceefadb41a9a4c95118c697e4c2
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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