Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate

HRID 610038Notes

Reaction equation

[OH:1][CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].Cl.[NH2:26][C@@H:27]([CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(N(C(C)C)CC)(C)C>C1COCC1>[C:31]([O:30][C:28](=[O:29])[C@@H:27]([NH:26][C:13]([O:1][CH2:2][C:3]12[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2)=[O:14])[CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([CH3:33])([CH3:34])[CH3:32]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 10.9 g (65.4 mmol) of (1-hydroxymethyl)adamantane and 10.6 g (65.4 mmol) of carbonyldiimidazole in 60 ml of THF were stirred at 50° C. for 1.5 h. 9.7 g (32.7 mmol) of tert-butyl (S)-2-amino-3-tert-butoxycarbonylaminopropionate hydrochloride in 25 ml of THF and 5.6 ml (32.7 mmol) of diisopropylethylamine were added, and the mixture was stirred at 60° C. for 4 h and allowed to stand at room temperature overnight. The solvent was removed in vacuo and the residue was chromatographed on silica gel using heptane/ethyl acetate (7/3). 8.7 g (59%) of the title compound were obtained as a colorless oil.

Workup

waitto stand at room temperature overnight
customThe solvent was removed in vacuo
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-14841a45a53042b98592e06f44239aaa
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998447

Reaction notes

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