Aluminium lithium hydride → N-trityl-1,3-dihydroxy-2-propanamine

HRID 863850Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@H:10]([CH2:39][OH:40])[N:11](O[Si](C(C)(C)C)(C)C)[C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C>[C:12]([NH:11][CH:10]([CH2:9][OH:8])[CH2:39][OH:40])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To dry ethyl ether (300 ml) is added with stirring lithium aluminum hydride (4.5 g; 0.12 mol) and cooled to 0° C. under nitrogen. The N-trityl-t-butyldimethylsilyloxy serine methyl ester (57 g; 0.12 mol) is added portionwise over 5 minutes as a solid. The reaction mixture is allowed to warm and stir for 30 minutes at 25° C. The mixture is quenched by slow addition of H2O (4.5 ml) at 0° C. followed by 15% NaOH (4.5 ml) and H2O (13.5 ml) at 25° C. After stirring for 3 hours, the mixture is filtered and the solid washed with THF. The combined filtrates are concentrated to which is added ether and petroleum ether to precipitate N-trityl-1,3-dihydroxy-2-propanamine which is used directly in Step D.

Workup

temperatureto warm
customThe mixture is quenched by slow addition of H2O (4.5 ml) at 0° C.
customfollowed by 15% NaOH (4.5 ml) and H2O (13.5 ml) at 25° C
stirringAfter stirring for 3 hours
filtrationthe mixture is filtered
washthe solid washed with THF
concentrationThe combined filtrates are concentrated to which
additionis added ether and petroleum ether
customto precipitate N-trityl-1,3-dihydroxy-2-propanamine which

Sources & evidence

ORD record: ord-117d4049f68d4c8196ec3a05e7bffe1e
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05561143

Reaction notes

Loading…