Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate → Benzyl 4-(2-(dimethylamino)ethoxy)piperidine-1-carboxylate

HRID 1091765Notes

Reaction equation

[CH3:1][N:2]([CH3:23])[C:3](=O)[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1>C1COCC1>[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 40 °C

Procedure

Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate (81) (4.5 g, 14.05 mmol) was dissolved in dry THF (50 mL), to this was added borane-methyl sulfide complex (10.53 mL, 21.07 mmol) and the reaction was stirred at 40° C. for 3 hours then at ambient temperature overnight. The gummy mixture was evaporated and was quenched with 2.0 N Na2CO3 (50 mL), extracted with EtOAc (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired material as a colourless liquid (4.00 g, 93% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.60-1.51 (2H, m), 1.88-1.78 (2H, m), 2.65 (6H, s), 2.97 (2H, t), 3.29-3.22 (2H, m), 3.54-3.48 (1H, m), 3.79-3.73 (2H, m), 3.85 (2H, t), 5.12 (2H, s), 7.36-7.28 (5H, m).

Workup

additionto this was added borane-methyl sulfide complex (10.53 mL, 21.07 mmol)
customat ambient temperature
customovernight
customThe gummy mixture was evaporated
customwas quenched with 2.0 N Na2CO3 (50 mL)
extractionextracted with EtOAc (3×75 mL)
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-c69d5b1bb3af454cbf82e8d51b8787f7
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129380B2

Reaction notes

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