Diethyl Ether → HCID 19420725, compound

HRID 1734698Notes

Reaction equation

C([N:3]([C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][CH:10]=1)[C:5](O)=[O:6])C.CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O.C1COCC1>[C:24]([NH:3][CH:4]([CH2:5][OH:6])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:13][CH:14]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of ethyl 2-[4-(benzoxazol-2-yl)benzyl]-N-trityl-glycine (8.8 g; 16 mmol), dry ether (80 ml) and dry THF (40 ml) is added lithium aluminum hydride (0.8 g; 21 mmol) at 0° C. The reaction is then cooled to 0° C. and 0.8 ml H2O is added slowly, followed by 0.8 ml of 15% NaOH and then 2.4 ml H2O. This is brought to 25° C. and stirred 15 hours. The reaction is filtered through a bed of celite and extracted with ether and THF. The flitrate is concentrated to an oil which solidifies upon treatment with MeOH and Et2O. The solid is recrystallized from MeOH to yield N-trityl-1-[4-(benzoxazol-2-yl)phenyl]-3-hydroxy-2-propanamine.

Workup

customThis is brought to 25° C.
filtrationThe reaction is filtered through a bed of celite and
extractionextracted with ether and THF
concentrationThe flitrate is concentrated to an oil which
customThe solid is recrystallized from MeOH

Sources & evidence

ORD record: ord-eb8f722ada31412ab04b93ef28061045
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05534532

Reaction notes

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