1-(tert-Butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid → HCID 66811101, compound

HRID 1099196Notes

Reaction equation

HRID 1099196 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]1[C:20](O)=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[OH:21][CH2:20][CH:9]1[CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

3

Reactant 1

HCID 450739411-(tert-Butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid

Product 1

HCID 66811101HCID 66811101, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid (416 mg, 1.36 mmol) in THF (2 ml) at 0° C. was added 1M borane-THF complex in THF (4.1 ml, 3.01 mmol). The reaction was warmed to rt and allowed to stir for 18 h. The reaction was cooled to 0° C., quenched with the careful addition of methanol, and concentrated in vacuo to yield tert-butyl 2-(hydroxymethyl)-3-phenylpiperidine-1-carboxylate (82%). HRMS (ES, M+Na) calcd for C17H25NO3: 314.1726, found: 314.1720. 1H NMR (400 MHz, CD3OD) δ 7.34-7.13 (m, 5H), 4.46 (m, 1H), 4.06 (d, J=13.0 Hz, 1H), 3.75 (m, 1H), 3.09 (m, 1.5H), 2.99 (m, 1.5H), 2.06 (m, 1H), 1.82 (m, 2H), 1.59 (m, 1H), 1.48 (s, 9H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with the careful addition of methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fec4a741f1c40be98c76663d73ccde1
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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