Lithium borohydride → HCID 12041756, compound

HRID 1263634Notes

Reaction equation

HRID 1263634 reaction equation
FC(F)(F)C1[NH:4][C:5]2[C:6]([N:27]=1)=[C:7]1[C:12](=[CH:13][CH:14]=2)[CH2:11][CH2:10][CH:9]([CH2:15][O:16]S(C2C=CC(C)=CC=2)(=O)=O)[O:8]1.[BH4-].[Li+]>C1COCC1>[NH2:4][C:5]1[C:6]([NH2:27])=[C:7]2[C:12]([CH2:11][CH2:10][CH:9]([CH2:15][OH:16])[O:8]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 12041755HCID 12041755, compound

Product 1

HCID 12041756HCID 12041756, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of toluene-4-sulfonic acid 2-trifluoromethyl-3,6,7,8-tetrahydro-9-oxa-1,3-diazacyclopenta[a]naphthalen-8-ylmethyl ester (500 mg, 2.11 mmol) in THF (50 mL) was added lithium borohydride (2.11 mL, 2 M, 4.22 mmol). The resulting solution was stirred for 30 min at 50° C. and then evaporated in vacuo to a residue. The residue was dissolved in ethyl acetate (100 mL) and then washed with water (2×30 mL), dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford 352 mg (86% yield) of the title compound: 1H NMR (400 MHz), CDCl3) δ1.90 (m, 2H), 2.78 (m, 2H), 3.18 (bs, 4H), 3.78 (m, 1H, OH), 3.82 (m, 2H), 4.18 (m, 1H), 6.33 (d, J=8 Hz), 6.42 (d, J=8 Hz); MS 195 [M+H]+.

Workup

  1. customevaporated in vacuo to a residue
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with water (2×30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2d90f62d4fb740a58af64635198dac86
Source dataset
uspto-grants-2003_04
Patent number
US06541502B1

Reaction notes

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