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Water → (5,5-Dimethyloxolan-2-yl)methanamine

HRID 335332
Notes
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Reaction equation

HRID 335332 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH3:10][C:8]1([CH3:11])[O:9][CH:5]([CH2:4][NH2:1])[CH2:6][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86695687HCID 86695687, compound

Product 1

HCID 75481615(5,5-Dimethyloxolan-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

5-(Azidomethyl)-2,2-dimethyltetrahydrofuran (22 g, 142 mmol) in THF (500 ml) was treated with Triphenylphosphine (39.0 g, 149 mmol) and t stirred for 5 mins. Water (50.0 ml) was added and the reaction mixture was heated at 80° C. for 4 hrs. The mixture was passed through Isolute® SCX-2 resin (200 g 0.67 mmol/g) eluting with MeOH (500 ml), DMSO (100 ml), 20% MeOH:DCM (500 ml), MeOH (500 ml) followed 7M ammonia in MeOH (500 ml). The ammonia layer was evaporated to dryness to afford the title compound.

Workup

  1. washeluting with MeOH (500 ml), DMSO (100 ml), 20% MeOH
  2. customThe ammonia layer was evaporated to dryness

Sources & evidence

ORD record
ord-2cf5a4f17b3a457a928f2591c5ae192c
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883819B2

Reaction notes

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