Water → HCID 57803569, compound

HRID 2103010Notes

Reaction equation

HRID 2103010 reaction equation
[NH2:1][CH2:2][C:3]1(O)[C:15]2[C:10](=[C:11]([CH3:19])[C:12]([CH3:18])=[C:13]([OH:17])[C:14]=2[CH3:16])[O:9][C:5]2([CH2:8][CH2:7][CH2:6]2)[CH2:4]1.[BH4-].[Na+].O>C(Cl)Cl.C(O)(C(F)(F)F)=O.C(O)(=O)C>[NH2:1][CH2:2][C:3]1[C:15]2[C:10](=[C:11]([CH3:19])[C:12]([CH3:18])=[C:13]([OH:17])[C:14]=2[CH3:16])[O:9][C:5]2([CH2:6][CH2:7][CH2:8]2)[CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57803521HCID 57803521, compound

Product 1

HCID 57803569HCID 57803569, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 23437676Trifluoroacetic acid acetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(aminomethyl)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol (277 mg) in DCM (10 mL) was slowly added to sodium borohydride (200 mg) in 4 mL of TFA-acetic acid, 1:1 at 0° C. The mixture was stirred at 0° C. for 2 h then poured into water and separated the DCM. The DCM was dried and evaporated. The residue was purified by silica gel column eluting with 7.5% MeOH in DCM to give 4-(aminomethyl)-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-6-ol (55 mg). 1H-NMR (300 MHz, CDCl3): δ=6.12 (s, 1H), 3.78 (s, 2H), 2.34-1.70 (3s+m, 18H) ppm. 13C-NMR (75 MHz, CDCl3): δ146.59, 145.56 137.14, 128.02, 124.51, 123.45, 120.62, 117.21, 76.24, 45.56, 36.07, 14.65, 12.85, 12.56, 12.33 ppm. MS: (m/z): 260 (M+H+).

Workup

  1. customseparated the DCM
  2. dry with materialThe DCM was dried
  3. customevaporated
  4. customThe residue was purified by silica gel column
  5. washeluting with 7.5% MeOH in DCM

Sources & evidence

ORD record
ord-8798228e23dd4389b2f684936600e99a
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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