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Benzylamine → tert-butyl (3R,4R)-4-(benzylamino)-3-hydroxypiperidine-1-carboxylate

HRID 2000307
Notes
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Reaction equation

HRID 2000307 reaction equation
[NH2:1][CH2:2][c:3]1[cH:8][cH:7][cH:6][cH:5][cH:4]1.[CH3:9][C:10]([O:13][C:14]([N:16]1[CH2:22][C@@H:21]([C@H:19]2[CH2:18][CH2:17]1)[O:20]2)=[O:15])([CH3:12])[CH3:11]>>[CH3:9][C:10]([O:13][C:14]([N:16]1[CH2:22][C@@H:21]([OH:20])[C@H:19]([NH:1][CH2:2][c:3]2[cH:8][cH:7][cH:6][cH:5][cH:4]2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])[CH3:11]
ParticipantsConditionsSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 55273474tert-butyl (1S,6R)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Product 1

HCID 67335553tert-butyl (3R,4R)-4-(benzylamino)-3-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 9812778Titanium(4+) fluorideReagentHCID 6342AcetonitrileSolventHCID 117669-PhenylanthraceneInternal standard

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-5c0ee80ab4634cb69d9e0621697f442a
Source dataset
39k HTE dataset from Pfizer
DOI
10.1038/s41557
Original link
View source

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes