Water → tert-butyl N-[1-(aminomethyl)cyclopentyl]carbamate

HRID 2281604Notes

Reaction equation

HRID 2281604 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 16740508tert-butyl N-(1-cyanocyclopentyl)carbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 16740809tert-butyl N-[1-(aminomethyl)cyclopentyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled 0° C. solution of (1-cyano-cyclopentyl)-carbamic acid tert-butyl ester (430 mg, 2.04 mmol) in dry THF (4.3 ml) under an atmosphere of argon is added dropwise 1.0 M LiAlH4 (6.13 ml, 6.13 mmol). The reaction mixture is allowed to warm to room temperature and stirred for 3.5 hours. The mixture is then re-cooled to 0° C. and cautiously quenched with water (0.4 ml): 15% NaOH (0.8 ml): water (1.2 ml) (1:2:3 eq). The resultant mixture is filtered through Celite® (filter material) to remove the inorganic solids and rinsed with MeOH. The filtrate is concentrated in vacuo, to yield a white solid, which is purified by chromatography on silica eluting with 30% MeOH in DCM to afford (1-Aminomethyl-cyclopentyl)-carbamic acid tert-butyl ester; [M+H]+ 215.

Workup

  1. temperatureThe mixture is then re-cooled to 0° C.
  2. customcautiously quenched with water (0.4 ml)
  3. filtrationThe resultant mixture is filtered through Celite® (filter material)
  4. customto remove the inorganic solids
  5. washrinsed with MeOH
  6. concentrationThe filtrate is concentrated in vacuo
  7. customto yield a white solid, which
  8. customis purified by chromatography on silica eluting with 30% MeOH in DCM

Sources & evidence

ORD record
ord-c7ab560451f44ad9872d36719adbb22e
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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