Hydrochloric Acid → tert-Butyl 2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

HRID 598534Notes

Reaction equation

HRID 598534 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH:18][O:19][CH3:20].C(N(CC)CC)C.Cl>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:16])[N:18]([O:19][CH3:20])[CH3:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acid

Product 1

HCID 21988510tert-Butyl 2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (RS)-1-(tert-butyloxycarbonyl)-2-piperidine carboxylic acid (2.64 g, 11.5 mmol) in dichloromethane (10 ml) was added sequentially N,O-dimethyl hydroxylamine (1.34 g, 13.7 mmol), triethylamine (6 ml, 43.0 mmol) and Py.Bop (6.60 g, 12.7 mmol). The resultant mixture was stirred at ambient temperature for 6 h, then diluted with dichloromethane (170 ml) and poured into 1M HCl (22 ml). The organic phase was separated and washed with saturated aqueous sodium hydrogen carbonate (3×25 ml) and brine (25 ml) then evaporated in vacuo. The resultant colourless oil was chromatographed on silica gel eluting with 20% ethyl acetate in hexane to give the title compound (2.43 g, 77%) as a colourless oil.

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated aqueous sodium hydrogen carbonate (3×25 ml) and brine (25 ml)
  3. customthen evaporated in vacuo
  4. customThe resultant colourless oil was chromatographed on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a5468a85e7a5476892bebf4b1123e9ac
Source dataset
uspto-grants-2011_03
Patent number
US07897618B2

Reaction notes

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