Methanol → 2-Amino-2-[2-(4-benzyloxy-phenyl)-ethyl]-propane-1,3-diol

HRID 490067Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH:22]C(=O)C)([CH2:20][OH:21])[CH2:18][OH:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.[OH-].[Li+]>O1CCCC1>[NH2:22][C:17]([CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)([CH2:20][OH:21])[CH2:18][OH:19]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of crude N-[3-(4-benzyloxy-phenyl)-1,1-bis-hydroxymethyl-propyl]-acetamide in a mixture of tetrahydrofuran, methanol, water (1/2/2) (450 ml/900 ml/900 ml) is added at room temperature lithium hydroxide (32.7 g, 1.36 mol, 8.0 eq). The reaction mixture is stirred at 55° C. for 5 hours, then extracted with ethyl acetate (500 ml) and washed with brine (2×300 ml), the combined organic layers are then dried with Na2SO4, filtered and concentrated under vacuum. 2-Amino-2-[2-(4-benzyloxy-phenyl)-ethyl]-propane-1,3-diol is isolated after crystallization using ethyl acetate (28.8 g, 97%).

Workup

extractionextracted with ethyl acetate (500 ml)
washwashed with brine (2×300 ml)
dry with materialthe combined organic layers are then dried with Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-7a4a25e1910e41449dc4ff5308c0173b
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528120B2

Reaction notes

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