Sodium Azide → (2R,4S,5S)-5-Azido-2-benzhydryl-tetrahydropyran-4-ol

HRID 78940Notes

Reaction equation

HRID 78940 reaction equation
[N-]=[N+]=[N-].[Na+].[N:5]([C@@H:8]1[CH2:13][O:12][C@H:11]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[OH:27])=[N+:6]=[N-:7]>CO>[N:5]([C@H:8]1[CH2:13][O:12][C@@H:11]([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:10][C@@H:9]1[OH:27])=[N+:6]=[N-:7]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 11716531(2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-ol

Product 1

HCID 11681112(2R,4S,5S)-5-Azido-2-benzhydryl-tetrahydropyran-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R,4R,7S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 8c (0.04 g, 0.15 mmol) was treated with NaN3 (0.05 g, 0.75 mmol) and NH4Cl (0.018 g, 0.33 mmol) (Procedure F) yielded (2R,4S,5S)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-ol 30b, 0.04 g (95%, [α]D=(+)108, c=1, MeOH).

Sources & evidence

ORD record
ord-cf07706c61a24e67ba51edc77db2ed36
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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