Di-tert-butyl dicarbonate → (6-Hydroxymethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester

HRID 32096Notes

Reaction equation

HRID 32096 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([CH2:12][OH:13])[CH:5]=[CH:4][C:3]1=2.[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O>C(Cl)Cl>[C:18]([O:17][C:15](=[O:14])[NH:1][CH:2]1[C:3]2[C:8](=[CH:7][C:6]([CH2:12][OH:13])=[CH:5][CH:4]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 18448553(5-Amino-5,6,7,8-tetrahydronaphthalen-2-yl)methanol

Product 1

HCID 58841393(6-Hydroxymethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanol (2.0 g, 11.28 mmol) in CH2Cl2 (20 mL) was added (BOC)2O (2.7 g, 12.41 mmol). The resulting mixture was stirred at RT under N2 gas for 2 h. Reaction mixture was quenched with sat. NH4Cl, the organic layer was isolated and washed with water, brine, dried over MgSO4 and evaporated in vacuo to give the final product. MS m/z: 278.12 (M+H). Calc'd. for C16H23NO3-277.36.

Workup

  1. customReaction mixture
  2. customwas quenched with sat. NH4Cl
  3. customthe organic layer was isolated
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d3093c98a1a6452d8b7c295a5c6a4ca5
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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