Methyl chloroformate → HCID 21077865, compound

HRID 1374740Notes

Reaction equation

HRID 1374740 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, compound

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 gun (1.36 g, 78%). 1H NMR (CDCl3) 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-3be7e0ffc3af48a0912e2208b4bd43ba
Source dataset
uspto-grants-2007_01
Patent number
US07166608B2

Reaction notes

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