9-Fluorenylmethyl chloroformate → HCID 86691262, compound

HRID 2037288Notes

Reaction equation

HRID 2037288 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3].[NH2:19][C@@:20]1([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:25][C:24](=[CH2:26])[C@@H:23]2[C@H:21]1[C@H:22]2[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH:17]1[C:18]2[CH:6]([CH2:5][O:4][C:2]([NH:19][C@@:20]3([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:25][C:24](=[CH2:26])[C@@H:23]4[C@H:21]3[C@H:22]4[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:3])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 86691263HCID 86691263, compound

Product 1

HCID 86691262HCID 86691262, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

Add solid 9-fluorenylmethyl chloroformate (3.15 g, 12.2 mmol) portion wise over 5 minutes to a stirred solution of diethyl (1S,2S,5R,6S)-2-amino-4-methylene-bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.8 g, 11.1 mmol) and sodium bicarbonate (2.04 g, 24.3 mmol) in tetrahydrofuran (28 mL) and water (8.4 mL) cooled to 0-5° C. After 1 hour, add water (10 mL) and extract with ethyl acetate (50 mL). Wash the extract with brine solution (20 mL), dry, filter and evaporate to a pale yellow oil (6.5 g). Purify by flash chromatography eluting with ethyl acetate:iso-hexane (10:90 to 20:80) to give a viscous colorless oil (4.58 g). Repurify by flash chromatography eluting with ethyl acetate:iso-hexane (20:80) to give a white semi-solid foam of title compound (4.22 g, 80%). MS (m/z): 476 (M+1).

Workup

  1. extractionextract with ethyl acetate (50 mL)
  2. washWash the
  3. extractionextract with brine solution (20 mL)
  4. customdry
  5. filtrationfilter
  6. customevaporate to a pale yellow oil (6.5 g)
  7. customPurify by flash chromatography
  8. washeluting with ethyl acetate:iso-hexane (10:90 to 20:80)

Sources & evidence

ORD record
ord-ba42021b09e442e0b0e238fd4b86dedd
Source dataset
uspto-grants-2013_11
Patent number
US08575214B2

Reaction notes

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