Water → 1-(3-Benzyl-3-azabicyclo[3.1.0]hexan-1-yl)methanamine

HRID 275197Notes

Reaction equation

HRID 275197 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH:18]2[C:16]([C:20]#[N:21])([CH2:17]2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[NH2:21][CH2:20][C:16]12[CH2:17][CH:18]1[CH2:19][N:14]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:15]2

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 121996873-Benzyl-3-azabicyclo[3.1.0]hexane-1-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 157134241-(3-Benzyl-3-azabicyclo[3.1.0]hexan-1-yl)methanamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (70 ml of a 1M solution in diethyl ether, 70 mmol) was added to a solution of 3-benzyl-1-cyano-3-azabicyclo[3.1.0]hexane (3.35 g, 16.9 mmol) in tetrahydrofuran (200 ml). After 18 hours at room temperature, the reaction mixture was treated sequentially with water (2.6 ml), sodium hydroxide (2.6 ml of a 15% aqueous solution), and water (7.8 ml). The mixture was filtered, and the filtrate was concentrated under reduced pressure to provide the title product as a viscous, slightly yellow oil (3.47 g, 100% yield), which was used without purification. 1H NMR (CDCl3): 7.20 (m, 5H), 3.54 (AB quartet, J=12 Hz, 2H), 2.92 (d, J=8 Hz, 1H), 2.87 (d, J=9 Hz, 1H), 2.81 (d, J=13 Hz, 1H), 2.59 (d, J=13 Hz, 1H), 2.33 (dd, J=8, 4 Hz, 1H), 2.25 (d, J=7 Hz, 1H), 1.10 (m, 1H), 0.97 (m, 1H), 0.30 (dd, J=8, 5 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-298f67873e934c8f8fca1e5a9da4f78d
Source dataset
uspto-grants-1995_02
Patent number
US05391763

Reaction notes

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