Fluorotrimethylsilane → trimethylsilyl (2S,4R)-N-(bromoacetyl)-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate

HRID 220748

Reaction equation

HRID 220748 reaction equation
C[Si](C)(C)[N:3]1[CH2:7][C@H:6]([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][C@H:4]1[C:13]([O:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Br:22][CH2:23][C:24](F)=[O:25].[Si](F)(C)(C)C>ClCCl>[Br:22][CH2:23][C:24]([N:3]1[CH2:7][C@H:6]([O:8][Si:9]([CH3:10])([CH3:11])[CH3:12])[CH2:5][C@H:4]1[C:13]([O:15][Si:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:25]

Participants

5

Reactant 3

HCID 9869FluorotrimethylsilaneHCID 5325486Bromoacetyl fluorideHCID 21632773(4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester

Product 1

HCID 46841619trimethylsilyl (2S,4R)-N-(bromoacetyl)-4-(trimethylsilyloxy)pyrrolidine-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a solution of trimethylsilyl (2S,4R)—N-(trimethylsilyl)-4-(trimethylsilyloxy)-pyrrolidine-2-carboxylate (6.95 g, 20.0 mmol) in 15 ml of anhydrous dichloromethane was drop wise added a solution of bromoacetyl fluoride (2.82 g, 20.0 mmol) in 5 ml of dichloromethane with vigorous stirring at room temperature. Exothermic reaction occurred with liberation of Me3SiF. The reaction mixture was stirred at room temperature for 2 h and then the reaction mixture was evaporated to dryness at reduced pressure, which gave 7.53 g (yield 95%) of trimethylsilyl (2S,4R)—N-(bromoacetyl)-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate as off-white solid: 1H-NMR (CDCl3) δ 0.04 (m, 9H), 0.21 (m, 9H), 1.80-2.4 (m, 2H), 3.3-3.6 (m, 1H), 3.61-3.80 (m, 2H), 4.3-4.6 (m, 2H); 13C-NMR (CDCl3) δ −0.27 (CSi), −0.01 (CSi), 26.94, 38.04, 55.71, 59.26, 70.33, 165.28, 171.82.

Workup

  1. customExothermic reaction
  2. stirringThe reaction mixture was stirred at room temperature for 2 h
  3. customthe reaction mixture was evaporated to dryness at reduced pressure, which

Sources & evidence

ORD record
ord-e8dce81b99b94990a1a1aaef992a7113
Source dataset
uspto-grants-2012_06
Patent number
US08203003B2

Linked notes

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