Dichloromethane → HCID 53954927, compound

HRID 1463281Notes

Reaction equation

HRID 1463281 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1.C(N(CC)CC)C.C(Cl)Cl>O1CCCC1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:24])[O:14][C@@H:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 1514398(R)-1-Boc-3-hydroxypiperidine

Product 1

HCID 53954927HCID 53954927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of (R)-(-)-N-tert-butoxycarbonyl-3-piperidinol (Reference Example 2) (23 g) in dry tetrahydrofuran (20 ml) were added 4-chlorophenyl isocyanate (1.43 ml) and triethylamine (1.87 mi) successively at room temperature with stirring, and then the mixture was stirred at room temperature for 10 hours. The reaction mixture was distilled under reduced pressure to give residues which was adsorbed on ca. 20 g of silica gel with employment of 50 ml of methylene chloride and purified through column chromatography (alumina, n-hexane:ethyl acetate =5:1) to give (R)-(+)-N-tert-butoxycarbonyl-3-piperidyl 4-chlorophenylcarbamate (3.07 g) of colorless prism crystal.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. distillationThe reaction mixture was distilled under reduced pressure
  3. customto give residues which
  4. custompurified through column chromatography (alumina, n-hexane:ethyl acetate =5:1)

Sources & evidence

ORD record
ord-9a60a4a61f8d418bbf329a012aef2548
Source dataset
uspto-grants-1994_04
Patent number
US05300515

Reaction notes

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