Methyl isothiocyanate → HCID 71258268, compound

HRID 2274314Notes

Reaction equation

[NH2:1][C@@H:2]1[C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:6]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:5]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][C@H:3]1O.[CH3:34][N:35]=[C:36]=[S:37]>>[CH3:34][NH:35][C:36]1[S:37][C@H:3]2[CH2:4][C@H:5]([CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:6]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C@H:7]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C@H:2]2[N:1]=1

Participants

Reactant 2

HCID 11167Methyl isothiocyanate

HCID 86727203(1R,2S,3R,4R,5R)-2-Amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol

Product 1

HCID 71258268HCID 71258268, compound

Procedure

The title compound was prepared via a synthetic sequence as described above Intermediate Example 7, starting form (1R,2S,3R,4R,5R)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol (0.150 g, 0.336 mmol) and methyl isothiocyanate (MeNCS) (0.049 g, 0.67 mmol). The crude product was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:20 to 1:3), affording (3aR,4R,5R,6R,7aS)-2-(mthylamino)-4,5-bisbenzyloxy-6-(benzyloxymethyl)-3a,4,5,6,7,7a-hexahydrobenzo[d]thiazole as a colorless oil (0.16 g, impure).

Workup

customThe crude product was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:20 to 1:3)

Sources & evidence

ORD record: ord-b9037a23ff9b4a3e9c7ca37f1ef36aa9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126957B2

Reaction notes

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