Water → 4'-(aminomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2'-[1,3]dioxolan]-5-one

HRID 1159439Notes

Reaction equation

HRID 1159439 reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][O:8][C:7]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[O:15][C:14]([CH3:24])([CH3:23])[CH2:13][CH2:12][C:11]=3[C:10]2=[O:25])[O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][CH:5]1[CH2:9][O:8][C:7]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[O:15][C:14]([CH3:23])([CH3:24])[CH2:13][CH2:12][C:11]=3[C:10]2=[O:25])[O:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 595143904'-(azidomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2'-[1,3]dioxolan]-5-one

Product 1

HCID 595143834'-(aminomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2'-[1,3]dioxolan]-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-(azidomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2′-[1,3]dioxolan]-5-one (0.012 mg, 0.035 mmol) in THF (1.0 mL) is added triphenylphosphine (0.033 mg, 0.13 mmol). The mixture is stirred at room temperature for 3 hour followed by addition of water (50 μL). The reaction is then stirred for another 16 hour at room temperature and solvent is removed under reduce pressure to yield a reside of 4′-(aminomethyl)-2,2-dimethyl-3,4-dihydro-2H,5H-spiro[benzo[h]chromene-6,2′-[1,3]dioxolan]-5-one as confirmed by LC/MS, which indicates the product, which has a molecular weight of 315 Da, is present in the crude residue along with triphenylphosphine oxide (a side product from the triphenylphosphine).

Workup

  1. stirringThe reaction is then stirred for another 16 hour at room temperature
  2. customsolvent is removed

Sources & evidence

ORD record
ord-a0e41d0375124947b46161693f44c170
Source dataset
uspto-grants-2010_10
Patent number
US07812051B2

Reaction notes

Loading…