Ammonium Chloride → HCID 66919828, compound

HRID 1971744Notes

Reaction equation

HRID 1971744 reaction equation
[C:1]([N:5]1[CH2:42][CH2:41][CH2:40][CH2:39][C:8]2[C:9]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C@@H:20]5[O:24][C:23]([CH3:26])([CH3:25])[O:22][C@H:21]5[C:27](OCC)=[O:28])[C:16]([O:32][CH3:33])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:43])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-].[NH4+].[Cl-]>C1COCC1.C(O)C>[C:1]([N:5]1[CH2:42][CH2:41][CH2:40][CH2:39][C:8]2[C:9]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C@@H:20]5[O:24][C:23]([CH3:26])([CH3:25])[O:22][C@@H:21]5[CH2:27][OH:28])[C:16]([O:32][CH3:33])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:43])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 70790601HCID 70790601, compound

Product 1

HCID 66919828HCID 66919828, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 680 mg of 21f in 20 ml of THF and 0.5 ml of ethanol was added dropwise 0.56 ml of a 2M solution of LiBH4 in THF. The reaction was stirred for 3 hr. The reaction was poured onto 5% NH4Cl solution, and the product was extracted into ethylacetate. The extract was dried and concentrated to provide 620 mg of product 21g which was used as is in the next step; Rf (Hept./ethyl acetate 1/1) 0.21. NMR (CDCl3) δ 7.35, 7.10, and 6.92 (3×m, 3, thienyl-H), 6.70 and 7.33 (2×s, 2, Ar—H); 5.10 (bd, 1, CHO), 4.65 (bm, 1, CH), 3.50-3.90 (bm, 6, CHO+CH2O+CH+CH2), 3.82 (s, 3, OCH3), 2.90+3.12 (2×bm, 2, CH2) 2.50 (b.m, 2, CH2) 1.60-2.05 (bm, 4, 2×CH2) 1.42 and 1.25 (2×s, 6, 2×CH3) 1.56 (s, 9, tertC4H9).

Workup

  1. extractionthe product was extracted into ethylacetate
  2. customThe extract was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-76a8474ec1d34223ac032b5540a30e64
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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