Water → (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-ylamine

HRID 1258168Notes

Reaction equation

HRID 1258168 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:11].C(N(CC)CC)C.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:19]([Si:23]([CH3:26])([CH3:25])[O:11][C@@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@H:2]1[NH2:1])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 69311541-Amino-2-indanol, trans-(-)-

Product 1

HCID 58450870(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-ylamine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(1R,2R)-1-amino-2-indanol (2.00 g) is suspended in 20 mL DCM and combined with triethylamine (3.61 mL) as well as DMAP (0.32 g). Then tert-butyldimethylchlorosilane (4.04 g in 2 mL CH2Cl2) is added. The reaction mixture is stirred for 16 h at RT and, once the reaction is complete, it is mixed with water, extracted with CH2Cl2 and the organic phase is freed from the solvent using the rotary evaporator. The residue is taken up in MeOH and isolate is added. After elimination of the solvent once again the mixture is purified by normal phase chromatography (CH2Cl2/EA). The product-containing fractions are combined and freed from the solvent using the rotary evaporator.

Workup

  1. extractionextracted with CH2Cl2
  2. customthe rotary evaporator
  3. customisolate
  4. additionis added
  5. customAfter elimination of the solvent once again the mixture is purified by normal phase chromatography (CH2Cl2/EA)
  6. customthe rotary evaporator

Sources & evidence

ORD record
ord-fd26d58fbd7d4ae9be9f1638420cb9f7
Source dataset
uspto-grants-2013_06
Patent number
US08466155B2

Reaction notes

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