Ammonium Hydroxide → 2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid

HRID 29132Notes

Reaction equation

HRID 29132 reaction equation
Br[CH:2]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([OH:16])([CH2:9]3)[CH2:7]1)[CH2:13]2)[C:3]([OH:5])=[O:4].[OH-].[NH4+:18]>>[NH2:18][CH:2]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([OH:16])([CH2:9]3)[CH2:7]1)[CH2:13]2)[C:3]([OH:5])=[O:4]

Participants

3

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 32746142-Bromo-2-(3-hydroxyadamantan-1-yl)acetic acid

Product 1

HCID 597889992-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid

Procedure

α-Bromo-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula Q) is then dissolved in ammonium hydroxide, preferably 30% ammonium hydroxide and the reaction mixture is heated preferably to 65° C. The reaction mixture is then concentrated to a solid. EtOH is then added and the reaction is again concentrated to yield a racemic mixture comprising (<aS)-<a-amino-3-hydroxytricyclo[3.3.1.1 3,7]decane-1-acetic acid (Formula V). See also Example 19 herein.

Workup

  1. concentrationThe reaction mixture is then concentrated to a solid
  2. additionEtOH is then added
  3. concentrationthe reaction is again concentrated

Sources & evidence

ORD record
ord-4a8db47570ef4d7eb375c486debbf309
Source dataset
uspto-grants-2008_09
Patent number
US07420079B2

Reaction notes

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