Benzyl Alcohol → N-(carbobenzyloxyaminosulfonyl)-2-piperidine-carboxylic acid methyl ester

HRID 743473Notes

Reaction equation

HRID 743473 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]1([CH2:14][OH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:17][O:18][C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][NH:22]1)=[O:20].Cl.[Cl-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH3:17][O:18][C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][N:22]1[S:2]([NH:5][C:6]([O:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])(=[O:4])=[O:3])=[O:20]

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 70918Chlorosulfonyl isocyanateHCID 13246231Methyl Pipecolinate Hydrochloride

Product 1

HCID 53700895N-(carbobenzyloxyaminosulfonyl)-2-piperidine-carboxylic acid methyl esterYield 102.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 7.36 ml (85 mmol) of chlorosulfonyl isocyanate in 180 ml of methylene chloride was added phenylmethanol (8.82 ml, 85 mmol) at 0° C. over a period of 35 minutes. After stirring the above solution for 2 hours at this temperature, a solution of 16.65 g (93 mmol) of 2-piperidinecarboxylic acid methyl ester hydrochloride in methylene chloride (500 ml) containing triethylamine (35.3 ml) was added at 0°-5° C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride (2×200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 31 g of N-(carbobenzyloxyaminosulfonyl)-2-piperidinecarboxylic acid methyl ester(Formula XIV: R=CH3 ; R1 =H; R2 and R3 together =-(CH2)4-) as a solid.

Workup

  1. additionwas added at 0°-5° C.
  2. stirringthe resulting mixture was stirred overnight
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with methylene chloride (2×200 ml)
  5. washthe combined organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0de5b2bd6434dd38230f7b0fc916738
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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