Sodium Bicarbonate → Methyl1-Boc-4-[[(R)-1-phenylethyl]amino]piperidine-3-carboxylate

HRID 736749Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH2:6][N:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][CH2:9][C:10]=1[NH:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])=[O:4].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(#N)C>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([NH:11][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:9][CH2:8][N:7]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(1-phenyl-ethyl amino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (4 g, 11.1 mmol) in acetic acid-acetonitrile (1:1, 80 mL) was treated with sodium triacetoxyborohydride (2.59 g, 12.2 mmol), and stirred for 5 h at 0° C. The reaction was cooled to 0° C. and neutralized with saturated aqueous sodium bicarbonate (5 mL). The organic layer was washed with brine (3×20 mL), then dried over MgSO4, filtered and concentrated to obtain a crude oil (3.6 g). The crude product was purified by Biotage Flash 40S chromatography, eluting with 1:1 ethyl acetate-hexanes, to provide 4-(1-phenyl-ethylamino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as a white solid (2.5 g, 62.5%). MS: 363 (M+H)+

Workup

washThe organic layer was washed with brine (3×20 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto obtain a crude oil (3.6 g)
customThe crude product was purified by Biotage Flash 40S chromatography
washeluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record: ord-bc72502901e440178f15945d90f21229
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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