4-Methylmorpholine → HCID 19010477, compound

HRID 1741670Notes

Reaction equation

HRID 1741670 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=2)[N:16]([CH2:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][C:29]([Cl:35])=[CH:30][CH:31]=3)[N:26]=2)[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7].CN1CCOCC1.[CH:43]1([O:48][C:49](Cl)=[O:50])[CH2:47][CH2:46][CH2:45][CH2:44]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([NH:23][C:49]([O:48][CH:43]3[CH2:47][CH2:46][CH2:45][CH2:44]3)=[O:50])[CH:21]=2)[N:16]([CH2:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][C:29]([Cl:35])=[CH:30][CH:31]=3)[N:26]=2)[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 2735892Cyclopentyl chloroformateHCID 19010476HCID 19010476, compound

Product 1

HCID 19010477HCID 19010477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of the amine from Step 2 in CH2Cl2 (4 ml) at r.t. was successively added N-methylmorpholine (130 μl, 3 eq.) followed by cyclopentylchloroformate (176 μl, 3 eq.). After 15 mins, the mixture was quenched with aq NH4Cl and worked up in the usual manner. Chromatography on silica gel (EtOAc/toluene, 1:9) afforded the title carbamate (170 mg).

Workup

  1. customat r.t.
  2. customthe mixture was quenched with aq NH4Cl

Sources & evidence

ORD record
ord-eb9c824da1d3418aac62842a78441837
Source dataset
uspto-grants-1994_08
Patent number
US05334597

Reaction notes

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