Diisopropylethylamine → HCID 86614174, compound

HRID 1098309Notes

Reaction equation

HRID 1098309 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([CH2:19][OH:20])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Cl:30][C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[Cl:30][C:31]([O:20][CH2:19][C@H:10]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 10891006(S)-(-)-2,3-Dibenzyloxy-1-propanol

Product 1

HCID 86614174HCID 86614174, compoundYield 200%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture consisting of 0.50 ml (1.98 mmol) of (S)-(−)-1,2-dibenzylglycerol and 0.69 ml (3.96 mmol) of N,N-diisopropylethylamine was dissolved in 5 ml of dichloromethane. The obtained solution was added dropwise to 5 ml of a dichloromethane solution containing 294 mg (0.99 mmol) of triphosgene under cooling on ice. The obtained mixture was stirred at a room temperature for 30 minutes. Thereafter, the reaction solution was concentrated, and the concentrate was then dissolved in 5 ml of dichloromethane, so as to obtain a dichloromethane solution of (R)-2,3-bis-benzyloxy-propyl chloroformate (1.98 mmol/5 ml).

Workup

  1. temperatureunder cooling on ice
  2. concentrationThereafter, the reaction solution was concentrated
  3. dissolutionthe concentrate was then dissolved in 5 ml of dichloromethane

Sources & evidence

ORD record
ord-05bd1f5ee63545f2978c6fa68565f4ab
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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