Benzyl chloroformate → HCID 58646747, compound

HRID 902000Notes

Reaction equation

HRID 902000 reaction equation
[NH2:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:12].C(=O)(O)[O-].[Na+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(O)C>[CH2:22]([O:21][C:19]([NH:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:12])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 12878373(2R,3R)-3-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 58646747HCID 58646747, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trans 3-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene (2.2 g, 72% pure) in ethanol (135 mL) stirring at room temperature under nitrogen was added sodium bicarbonate (2.2 g) and benzyl chloroformate (2.12 mL). After 4 h, the reaction mixture was concentrated under reduced pressure and purified by silica gel chromatography eluting with a step-wise gradient of 30-70% ethyl acetate in hexane to provide the title compound (2.0 g) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel chromatography
  3. washeluting with a step-wise gradient of 30-70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-20a91b3a94014128aa98ddf807c1f013
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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