Triethylamine → HCID 86753199, compound

HRID 399042Notes

Reaction equation

HRID 399042 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C.Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(OCC)C>[CH2:33]([O:32][C:30]([NH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][CH:14]=1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 53969017HCID 53969017, compound

Product 1

HCID 86753199HCID 86753199, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (±) cis 1-amino-2-(4-benzylphenoxymethyl)cyclopentane (0.9 g, 3.20 mmol) in dry diethyl ether (100 ml) containing triethylamine (0.89 ml, 6.4 mmol) was added ethyl chloroformate (0.40 ml, 4.16 mmol) under argon. After stirring at room temperature for 2.5 h the reaction was quenched with ice water and the pH of the aqueous layer was adjusted to 7 by addition of dilute hydrochloric acid. The organic layer was separated and the aqueous phase was extracted with diethyl ether (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to give a pale yellow oil (1.16 g) which was used in the next stage without further purification.

Workup

  1. customwas quenched with ice water
  2. additionthe pH of the aqueous layer was adjusted to 7 by addition of dilute hydrochloric acid
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with diethyl ether (2×50 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59f2df865aa24aa3b888545f09835772
Source dataset
uspto-grants-1998_10
Patent number
US05817698

Reaction notes

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