Water → (S)-5-bromo-2,3-dihydro-1H-inden-1-amine

HRID 2046532Notes

Reaction equation

HRID 2046532 reaction equation
[N:1]([C@@H:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+]>C1COCC1>[Br:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[C@@H:4]([NH2:1])[CH2:5][CH2:6]2

Participants

6

Reactant 4

HCID 962Water2×HCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 86638803(S)-1-Azido-5-bromo-indan

Product 1

HCID 28206724(S)-5-bromo-2,3-dihydro-1H-inden-1-amineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-Azido-5-bromo-2,3-dihydro-1H-indene (8.09 g, 34.0 mmol) was dissolved in THF (155 ml), then water (17.2 ml) was added, followed by triphenylphosphine (9.8 g, 37.4 mmol). To this mixture, potassium hydroxide (1.0 N, 34.0 ml, 34.0 mmol) was added drop by drop below 25° C. and stirring continued over night at RT. The reaction mixture was then poured into H2O (150 ml) and extracted with EtOAc (2×100 ml). The organic layers were dried over MgSO4, filtered and concentrated in vacuo to give a crude product (17.34 g), which was purified by flash chromatography (silica gel, 100 g, 0% to 40% MeOH in CH2Cl2) to yield the title compound (5.81 g, 81%) as light yellow oil. MS: 211 (M+, 1Br).

Workup

  1. waitcontinued over night at RT
  2. extractionextracted with EtOAc (2×100 ml)
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product (17.34 g), which
  7. customwas purified by flash chromatography (silica gel, 100 g, 0% to 40% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6b3350098518417a997710dc4a73784e
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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