Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)borane → (R)-4-[(4-bromophenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726129Notes

Reaction equation

HRID 1726129 reaction equation
B(Cl)([C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([C:36](=[O:44])[C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([O:27][C:28]([N:30]1[CH2:31][CH2:32][CH:33]([C@H:36]([C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)[OH:44])[CH2:34][CH2:35]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 13515837Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)boraneHCID 228905261-Boc-4-(4-Bromobenzoyl)piperidine

Product 1

HCID 68972488(R)-4-[(4-bromophenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester

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 to give (R)-4-[(4-bromophenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester (ee 82% determined by both chiral HPLC and Mosher ester) as a crystalline solid (2.22 g, 54%) following work-up and purification. This material was recrystallized (CH2Cl2/hexane) five times to provide a white solid (1.27 g, 35%) with 95% ee.

Sources & evidence

ORD record
ord-14c4347d5a0941f489cde35b8222d8bd
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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