Lithium borohydride → HCID 11404536, compound

HRID 268667Notes

Reaction equation

HRID 268667 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([CH2:20][CH3:21])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[CH:17][CH:16]=[CH:15][C:14]=3[Br:19])C.[BH4-].[Li+]>O1CCCC1>[Br:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[NH:12][C:11]1[C:6]([CH2:5][CH2:4][OH:3])([CH2:20][CH3:21])[O:7][CH2:8][CH2:9][C:10]2=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69198866HCID 69198866, compound

Product 1

HCID 11404536HCID 11404536, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (8-bromo-1-ethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester (1.03 g, 2.8 mmol) in tetrahydrofuran at room temperature was added 2.0 M solution of lithium borohydride in tetrahydrofuran. The mixture was heated to reflux for 5 hours. It was quenched with 5% HCl solution, followed by saturated sodium bicarbonate. It was extracted with ethyl acetate, extracts were dried over magnesium sulfate, and it was evaporated to dryness. Crystallization with diethyl ether afforded 0.682 g (75%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ 8.01 (br, 1H), 7.45 (d, 1H), 7.32 (d, 1H), 7.00 (t, 1H), 4.07 (m, 1H), 3.99 (m, 1H), 3.72 (m, 1H), 3.67 (m, 1H), 2.87 (m, 1H), 2.75 (dt, 1H), 2.68 (dd, 1H), 2.24 (m, 1H), 2.08 (m, 1H), 2.02 (m, 1H), 1.93 (m, 1H), 0.94 (t, 3H); ESI (+) MS m/e=324 (MH+), ESI (−) MS m/e=322 (MH−).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. customIt was quenched with 5% HCl solution
  4. extractionIt was extracted with ethyl acetate, extracts
  5. dry with materialwere dried over magnesium sulfate, and it
  6. customwas evaporated to dryness
  7. customCrystallization with diethyl ether

Sources & evidence

ORD record
ord-ba9c938bc14847b68aeab948bd6bd690
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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