Methanol → trans-3-Amino-4-hydroxycyclopentene deoxycholate

HRID 1632343Notes

Reaction equation

[NH2:1][C@H:2]1C[CH2:5][C@H:4](O)[CH2:3]1.[CH3:8][C@@H:9]([C@@H:15]1[C@@:19]2([CH3:35])[C@@H:20]([OH:34])[CH2:21][C@@H:22]3[C@@:27]4([CH3:33])[CH2:28][CH2:29][C@@H:30]([OH:32])[CH2:31][C@H:26]4[CH2:25][CH2:24][C@H:23]3[C@@H:18]2[CH2:17][CH2:16]1)[CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH3:36][OH:37]>>[NH2:1][C@H:2]1[C@H:36]([OH:37])[CH2:5][CH:4]=[CH:3]1.[CH3:8][C@@H:9]([C@@H:15]1[C@@:19]2([CH3:35])[C@@H:20]([OH:34])[CH2:21][C@@H:22]3[C@@:27]4([CH3:33])[CH2:28][CH2:29][C@@H:30]([OH:32])[CH2:31][C@H:26]4[CH2:25][CH2:24][C@H:23]3[C@@H:18]2[CH2:17][CH2:16]1)[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

Reactant 3

HCID 887Methanol2×

HCID 222528Deoxycholic Acid

HCID 42614395(1S,3S)-3-Aminocyclopentan-1-ol

Product 1

HCID 12943949trans-3-Amino-4-hydroxycyclopentene deoxycholate

Procedure

A 49.5 g (0.50 M) quantity of dl trans-3-amino-hydroxycyclopentane dissolved in about 100-200 ml of methanol and 98 g (0.25M) of deoxycholic acid dissolved in about 200-300 ml of methanol are mixed and allowed to crystallize for several hours. The crystals of trans-3-amino-4-hydroxycyclopentene are collected by filtration and washed three times with some portions of methanol. There is obtained 105 g of trans-3-amino-4-hydroxycyclopentene deoxycholate as light beige crystals, m.p. 195°-197° (dec). The mother liquors are saved for Step 2.

Workup

additionare mixed
customto crystallize for several hours
filtrationThe crystals of trans-3-amino-4-hydroxycyclopentene are collected by filtration
washwashed three times with some portions of methanol

Sources & evidence

ORD record: ord-433c38c0d74040f982c1ca5c65ef10f6
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04474968

Reaction notes

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