Sodium Hydroxide → 1-Amino-4-phenylbutan-2-ol

HRID 389073

Reaction equation

HRID 389073 reaction equation
[OH:1][CH:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]#[N:4].NCC(O)CC(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O.CCOCC>[NH2:4][CH2:3][CH:2]([OH:1])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 109098692-Hydroxy-4-phenylbutanenitrile2×HCID 183564841-Amino-4-methylpentan-2-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 157609871-Amino-4-phenylbutan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

1b is prepared from 2-hydroxy-4-phenylbutanenitrile according to the protocol described for 1a; LiAlH4 (6.2 g, 163 mmol), Et2O (120 ml), 2-hydroxy-4-phenylbutanenitrile (12.4 g, 77 mmol), H2O (6.2 ml), 15% aqueous NaOH (6.2 ml) and H2O (18 ml). The product, an orange oil, is used with no other purification (11 g, 87%); 1H NMR (100 MHz, CDCl3) δ: 1.80 (m, 3H), 2.65 (m, 4H), 3.62 (m, 3H), 7.21 (s, 5H); 13C NMR (25 MHz, CDCl3) δ: 33.98, 36.25, 70.92, 125.46, 128.04, 141.74. Analysis calculated for C10H15NO: C, 72.69; H, 9.15; N, 8.48. Experimental: C, 72.45; H, 9.33; N, 8.24.

Workup

  1. customThe product, an orange oil, is used with no other purification (11 g, 87%)

Sources & evidence

ORD record
ord-7b088b05baf24839abab4d60dcfe0ad9
Source dataset
uspto-grants-2013_02
Patent number
US08378098B2

Linked notes

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