Methyl chloroformate → HCID 21077865, compound

HRID 750467Notes

Reaction equation

HRID 750467 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH:14]1[CH2:19][CH2:20][OH:21])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:2]([O:4][CH3:5])=[O:3])[CH2:15][CH:14]1[CH2:19][CH2:20][OH:21])=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 18933038tert-Butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 21077865HCID 21077865, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl chloroformate (0.52 ml, 6.73 mmol) in dichloromethane (5 ml) was added dropwise over 0.1 h to a stirred solution of (RS)-1-(tert-butyloxycarbonyl)-2-(2-hydroxyethyl)piperazine (D6) (1.4 g, 6.09 mmol) and triethylamine (1.7 ml, 12.2 mmol) in dichloromethane (45 ml) at 0° C. under argon. The resultant mixture was stirred at room temperature for 18 h, washed with saturated sodium hydrogen carbonate and the organic layer dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 10-100% ethyl acetate in hexane to give the title compound as a colourless gum (1.36 g, 78%). 1H NMR (CDC13)δ: 1.48 (9H, s), 1.60-1.95 (2H, m), 2.80-3.00 (2H, m), 3.05-3.45 (2H, m), 3.50-3.70 (2H, m), 3.70 (3H, s), 3.75-4.45 (4H, m).

Workup

  1. washwashed with saturated sodium hydrogen carbonate
  2. dry with materialthe organic layer dried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 10-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-eaad63d8d99c42fb84ea727678fb5d36
Source dataset
uspto-grants-2008_07
Patent number
US07405217B2

Reaction notes

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