Cesium carbonate → (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-vinylphenyl)cyclopentanecarboxylate

HRID 1511865Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@:12]1([C:24]([O:26][CH3:27])=[O:25])[CH2:16][CH2:15][C@@H:14]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][C:29]1(C)C(C)(C)OB(C=C)O1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:8][C:9]([NH:11][C@:12]1([C:24]([O:26][CH3:27])=[O:25])[CH2:16][CH2:15][C@@H:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:28]=[CH2:29])=[CH:19][CH:18]=2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a 60-mL microwave vial was suspended (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-bromophenyl)cyclopentanecarboxylate (1.1 g, 2.54 mmol) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.431 g, 2.80 mmol) and Cs2CO3 (2.487 g, 7.63 mmol) in DME (30 ml) and Water (7.50 ml). The reaction vessel was purged with nitrogen for 5 minutes. PdCl2(dppf) (0.186 g, 0.254 mmol) was added and the reaction vessel was purged with nitrogen one more time. The reaction mixture was heated to 120° C. in microwave for 30 minutes. The product ((1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-vinylphenyl)cyclopentanecarboxylate (705 mg, 1.858 mmol, 73.0% yield)) was isolated by FCC as a lightly colored oil.

Workup

customThe reaction vessel was purged with nitrogen for 5 minutes
customthe reaction vessel was purged with nitrogen one more time

Sources & evidence

ORD record: ord-97ca3723ad0f46018cbeb4e9b93927dd
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217027B2

Reaction notes

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