tert-butyl N-[(1S,4R)-4-hydroxycycloheptyl]carbamate → (1S,4R)-4-aminocycloheptan-1-ol

HRID 1631451Notes

Reaction equation

HRID 1631451 reaction equation
[OH:1][C@@H:2]1[CH2:8][CH2:7][CH2:6][C@H:5]([NH:9]C(=O)OC(C)(C)C)[CH2:4][CH2:3]1>Cl.O1CCOCC1>[NH2:9][C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:2]([OH:1])[CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 69723966tert-butyl N-[(1S,4R)-4-hydroxycycloheptyl]carbamate

Product 1

HCID 15458399(1S,4R)-4-aminocycloheptan-1-ol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A sample of 23B (0.070 g, 0.31 mmol) was dissolved in 2 mL of 4M HCl in dioxane and stirred 1.5 h. The reaction was concentrated under reduced pressure to afford 23C.HCl (51 mg, quantitative yield) as a white solid. This material was used without characterization in the subsequent step.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-48f17da55f8149b284b04473bae9b1e7
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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