(-)DIP-Chloride → HCID 68970728, compound

HRID 1726124

Reaction equation

HRID 1726124 reaction equation
B(Cl)([C@H]1[C@H](C)C2C(C)(C)C(CC2)C1)[C@H]1[C@H](C)C2C(C)(C)C(CC2)C1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([C:38](=[O:46])[C:39]2[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[C:25]([O:29][C:30]([N:32]1[CH2:33][CH2:34][CH:35]([C@@H:38]([C:39]2[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=2)[OH:46])[CH2:36][CH2:37]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 16212015(-)DIP-ChlorideHCID 22890526tert-Butyl 4-(4-bromobenzoyl)piperidine-1-carboxylate

Product 1

HCID 68970728HCID 68970728, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (−)-DIP-chloride™ (6.42 g, 20.0 mmol) in THF (10 mL) at 0° C. was added 4-(4-bromobenzoyl)-piperidine-1-carboxylic acid tert-butyl ester (3.68 g, 10.0 mmol). The mixture was stirred at room temperature for 29 hours. Aqueous work-up and purification gave (S)-4-[(4-bromophenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester (ee 78% determined by both chiral HPLC and Mosher ester) as a crystalline solid (2.22 g, 54%). This material was recrystallized (CH2Cl2/hexane) three times to provide (S)-4-[(4-bromophenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (1.29 g, 35%) with ee of 96%.

Workup

  1. customAqueous work-up and purification

Sources & evidence

ORD record
ord-2eec1b163dc645e89f4a70ae50830d3b
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Linked notes

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