Sodium borohydride → 1H-Indene-1-methanol, 1-amino-2,3-dihydro-

The product of Example 93A (0.292 g, 1.423 mmol) and sodium borohydride (0.275 g, 7.113 mmol) were reacted in 1:3 v/v water/ethanol (7 mL), at reflux for 4 hours. The reaction was concentrated by rotary evaporation the partitioned between water (5 mL), ethyl ether (20 mL), 1N aqueous sodium hydroxide (0.712 mL). Solid sodium chloride was added to saturate the aqueous phase and separate the phases. The aqueous phase was extracted with ethyl ether (2×25 mL). The combined ethereal extracts were washed with brine (25 mL), dried over potassium carbonate, filtered, and concentrated by rotary evaporation to afford the title compound (0.197 g, 1.209 mmol, 85%). NMR (300 MHz, DMSO-D6) δ ppm 1.64-1.80 (m, 1 H) 1.85 (s, 2 H) 2.16-2.31 (m, 1 H) 2.63-2.91 (m, 2 H) 3.30 (d, J=5.52 Hz, 2 H) 4.74 (t, J=5.52 Hz, 1 H) 6.80-7.63 (m, 4 H). MS (DCI) m/z 164 (M+H)+, 181 (M+NH4)+.

1. temperatureat reflux for 4 hours
2. concentrationThe reaction was concentrated by rotary evaporation the
3. custompartitioned between water (5 mL), ethyl ether (20 mL), 1N aqueous sodium hydroxide (0.712 mL)
4. additionSolid sodium chloride was added
5. concentrationto saturate the aqueous phase
6. customseparate the phases
7. extractionThe aqueous phase was extracted with ethyl ether (2×25 mL)
8. washThe combined ethereal extracts were washed with brine (25 mL)
9. dry with materialdried over potassium carbonate
10. filtrationfiltered
11. concentrationconcentrated by rotary evaporation

ORD record

ord-2fc20988b46f469d9e62b32b24eeab40

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236950B2